Synthesis of 5-substituted cyclopropyl caffeate ethyl esters derivatives

MARTINEZ, MARIO D.; SIMOES, C. M. O.; BERNARDES, L. S. C.; REGINATTO, F. H.; BURTON, GERARDO; DURÁN, FERNANDO J.

Ouro Preto

Simposio; 5th Brazilian Symposium on Medicinal Chemistry; 2010

Brazilian Chemical Society (SBQ). Division of Medicinal Chemistry

Caffeic acid (1) and its esters are phenolic compounds with a very large distribution in nature. These compounds present activities as antibacterial, antiviral, antitumor and as neurotoxin inhibitors. 1-3       The cyclopropyl moiety is a bioisoster of the carbon-carbon double bond functionality that preserves its structural rigidity but increases metabolic stability. Thus, introduction of this isosteric replacement in biologically active compounds may result in beneficial changes in their activity4. The caffeic acid skeleton appeared as an interesting template to perform this replacement, considering the activities associated with the parent compound and its derivatives. The aim of this work was to prepare series of 5-substituted cyclopropyl caffeate ethyl esters (2) and (3) to evaluate their biological activities